Linear planning and decision-making models assume a level of predictability that is uncommon today. Such models inadequately address the complex variables found in higher education. When academic organizations adopt paired-down business strategies, they restrict their own vision. They fail to harness emerging opportunities or learn from their own mistakes. Better models do exist, however, and can help educational planners improve planning practice. Strategies employed in design professions (like architecture) incorporate non-linear, iterative, synthesizing processes. Iterative techniques can help organizations (and their leaders) understand and deal with change in proactive ways. This article defines and illustrates iterative planning strategies and metaphors that may help, such as decision-making spirals, interactive learning methods, design thinking, improvisation, chaos theory, and the collaborative design-studio format. (Contains 7 figures.)